JP4504135B2 - t−ブタノールの製造方法 - Google Patents
t−ブタノールの製造方法 Download PDFInfo
- Publication number
- JP4504135B2 JP4504135B2 JP2004242901A JP2004242901A JP4504135B2 JP 4504135 B2 JP4504135 B2 JP 4504135B2 JP 2004242901 A JP2004242901 A JP 2004242901A JP 2004242901 A JP2004242901 A JP 2004242901A JP 4504135 B2 JP4504135 B2 JP 4504135B2
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- tba
- isobutene
- crude
- last
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims description 192
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 100
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 229930195733 hydrocarbon Natural products 0.000 claims description 28
- 150000002430 hydrocarbons Chemical class 0.000 claims description 28
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 17
- 238000001704 evaporation Methods 0.000 claims description 11
- 230000008020 evaporation Effects 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 238000001577 simple distillation Methods 0.000 claims description 2
- 230000001771 impaired effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 9
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical class CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011102 hetero oligomerization reaction Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/12—Monohydroxylic acyclic alcohols containing four carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
n−ブタン:8.2質量部
イソブタン:2.3質量部
1−ブテン:29.8質量部
2−ブテン(シス+トランス):14.3質量部
イソブテン:45.4質量部
このラフィネート流を、実験室用−試験プラント中で水及び可溶化剤としての返送−TBAと反応させた。4つの反応器を直列接続し、その際に、第一の反応器を循環路反応器として運転した。反応器1〜3は、その都度250〜450mlの触媒体積を有する触媒固定床段階からなっており、第4の反応器を950mlの触媒体積で運転した。触媒として、H+−形のAmberlyst 35もしくはAmberlyst 15を使用した。生成物流を、ガスクロマトグラフィーにより分析した。成分:n−ブタン、イソブタン、1−ブテン、2−ブテン(シス+トランス)を、総和で残分−C4として列挙した。記載された組成は、20〜30時間の試験期間後に達成されることができた準定常の平衡における生成物排出物に基づいていた。プラント中の圧力は、12bar(絶対)であり、実験室用塔は50mmの直径を有し、かつ6bar絶対で運転した。第一の反応器は55℃の入口温度で、別の3つ全ての反応器は50℃で運転した。個々の試験をより良好に比較するために、流れ(20)を常に、混合物中で10.4質量部の含水量に調節されるように付加的な水で補充した。このことは、第一の反応器での高められたプロセス水添加に相当する。
例1(本発明による)
次の第1表中の流れ番号は、図1中のそれに相当する。蒸発工程(11)のために、加熱された実験室用圧力容器を使用した。ラフィネート流(ラフィネートI)の供給は0.3kg/hであった。
例2(比較)
次の第2表中の流れ番号は図1中のそれに相当する。質量部で記載されている。ラフィネート流(ラフィネートI)の供給は0.3kg/hであった。転化率への効果を調査するために、付加的な蒸発なしで作業した。
例3(本発明による)
次の第3表中の流れ番号は図2のそれに相当する。その都度質量部で記載されている。ラフィネート流(ラフィネートI)の供給は0.3kg/hであった。
例の比較:
例1(本発明による)における単純な蒸発により並びに例3(本発明による)による新規の接続により、転化率を、例2(比較例)による反応器の従来の連続接続と比較して明らかに上昇させることができた。
Claims (5)
- 水、t−ブタノール(TBA)及びイソブテン含有炭化水素混合物を含有している混合物を、少なくとも2つの反応器を有する反応器カスケード中で、酸性触媒上で30〜120℃で反応させ、引き続いて未反応の炭化水素類を蒸留により分離することにより、t−ブタノール(TBA)を製造する方法において、
反応器カスケードの最後の反応器ではない少なくとも1つの反応器の反応器排出物からTBAの一部を蒸留もしくは精留により分離してから、TBAの減損された反応器排出物を次の反応器へ導き、その際に、TBAの分離を、次の反応器又は最後の反応器へ送られるTBAの減損された生成物が、10〜50質量%のTBA含量を有するように行うことを特徴とする、t−ブタノール(TBA)の製造方法。 - 反応器カスケードの最後の反応器ではない反応器の反応搬出物からのTBAの一部の分離を蒸留もしくは精留により行い、その際に、TBAの減損された生成物流を次の反応器へ送り、TBAの豊富化された生成物流を次の反応器の排出物と一緒に、粗−TBAを後処理するための塔(粗−TBA−塔)中へ供給する、請求項1記載の方法。
- TBAの一部の分離を、フラッシュ蒸発/単純な蒸発又は単蒸留により行う、請求項1又は2記載の方法。
- 反応器カスケードの最後の反応器ではない反応器からの反応器排出物を、完全にか又は部分的に、最後の反応器の排出物と一緒に粗−TBAを分離するための塔(粗−TBA−塔)中へ供給し、未反応イソブテンを有する炭化水素類を含有する留出液の一部及び粗−TBA−塔の粗−TBAとしての缶出液の一部を最後の反応器中へ導入する、請求項1記載の方法。
- 反応器カスケードの最後の反応器ではなく、かつ15質量%未満のイソブテン含量を有する少なくとも1つの反応器の反応器排出物からのTBAの分離を行う、請求項1から4までのいずれか1項記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10338581A DE10338581A1 (de) | 2003-08-22 | 2003-08-22 | Verfahren zur Erzeugung von tert.-Butanol |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005068150A JP2005068150A (ja) | 2005-03-17 |
JP4504135B2 true JP4504135B2 (ja) | 2010-07-14 |
Family
ID=34042243
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004242901A Expired - Fee Related JP4504135B2 (ja) | 2003-08-22 | 2004-08-23 | t−ブタノールの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7026519B2 (ja) |
EP (1) | EP1508558B1 (ja) |
JP (1) | JP4504135B2 (ja) |
KR (1) | KR101122516B1 (ja) |
CN (1) | CN100358852C (ja) |
DE (1) | DE10338581A1 (ja) |
ES (1) | ES2397384T3 (ja) |
SG (1) | SG118238A1 (ja) |
TW (1) | TW200513537A (ja) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
DE10241762A1 (de) * | 2002-09-10 | 2004-03-18 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von wasserfreiem tert.-Butanol |
DE10260991A1 (de) * | 2002-12-24 | 2004-07-08 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von tert.-Butanol mittels Reaktivrektifikation |
US20050171393A1 (en) | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
WO2005021468A1 (en) | 2003-07-15 | 2005-03-10 | Grt, Inc. | Hydrocarbon synthesis |
US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
DE102004030943B4 (de) | 2004-06-26 | 2013-10-02 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von tert.-Butanol aus Isobuten-haltigen Kohlenwasserstoffgemischen |
MY142026A (en) * | 2004-12-17 | 2010-08-16 | Mitsubishi Rayon Co | Method for producing tert-butyl alcohol |
SG158189A1 (en) | 2005-11-01 | 2010-01-29 | Asahi Kasei Chemicals Corp | Processes for production of isobutene and tertiary butanol |
EP1993979A4 (en) | 2006-02-03 | 2011-07-06 | Grt Inc | CONTINUOUS PROCESS FOR CONVERTING NATURAL GAS TO LIQUID HYDROCARBONS |
UA95943C2 (ru) | 2006-02-03 | 2011-09-26 | ДжиАрТи, ИНК. | Отделение легких газов от галогенов |
EA017699B1 (ru) | 2007-05-24 | 2013-02-28 | Грт, Инк. | Зонный реактор с обратимым захватыванием и высвобождением галогеноводородов |
US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
SG192538A1 (en) | 2008-07-18 | 2013-08-30 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
US8394900B2 (en) * | 2010-03-18 | 2013-03-12 | Syntroleum Corporation | Profitable method for carbon capture and storage |
US8558036B2 (en) | 2010-11-15 | 2013-10-15 | Saudi Arabian Oil Company | Dual phase catalysts system for mixed olefin hydrations |
US8815050B2 (en) | 2011-03-22 | 2014-08-26 | Marathon Gtf Technology, Ltd. | Processes and systems for drying liquid bromine |
US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
US8865950B2 (en) * | 2011-08-10 | 2014-10-21 | Saudi Arabian Oil Company | Olefin hydration process with an integrated membrane reactor |
US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
CN103804139B (zh) * | 2012-11-14 | 2016-05-11 | 上海华谊丙烯酸有限公司 | 叔丁醇的制备方法 |
US9732018B2 (en) | 2014-02-11 | 2017-08-15 | Saudi Arabian Oil Company | Process for production of mixed butanols and diisobutenes as fuel blending components |
US11097998B1 (en) | 2020-03-02 | 2021-08-24 | Saudi Arabian Oil Company | Process for production of mixed butanol and diisobutenes as fuel blending components |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60233024A (ja) * | 1984-05-02 | 1985-11-19 | Mitsui Toatsu Chem Inc | 第3級ブチルアルコ−ルの製造方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2538036A1 (de) * | 1975-08-27 | 1977-03-17 | Basf Ag | Verfahren zur herstellung von tert.- butanol |
JPS6051451B2 (ja) | 1978-11-06 | 1985-11-14 | 三菱レイヨン株式会社 | 第3級ブチルアルコ−ルの製造法 |
JPS6058893B2 (ja) * | 1979-04-27 | 1985-12-23 | 東亜燃料工業株式会社 | 第3級アルコ−ルの製造方法 |
JPS6058894B2 (ja) * | 1979-06-26 | 1985-12-23 | 東亜燃料工業株式会社 | 第3級アルコ−ルの製造法 |
JPS5610124A (en) * | 1979-07-05 | 1981-02-02 | Sumitomo Chem Co Ltd | Preparation of tert-butyl alcohol |
JPS5634643A (en) | 1979-08-31 | 1981-04-06 | Toa Nenryo Kogyo Kk | Preparation of tertiary butyl alcohol |
DE4322712A1 (de) * | 1993-07-08 | 1995-01-12 | Huels Chemische Werke Ag | Verfahren zur Durchführung chemischer Reaktionen in Reaktionsdestillationskolonnen |
JPH11193255A (ja) * | 1997-12-26 | 1999-07-21 | Mitsubishi Rayon Co Ltd | 第3級ブチルアルコールの製造方法 |
DE10330710A1 (de) | 2002-12-19 | 2004-07-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von tert.-Butanol |
EP1431264B1 (de) * | 2002-12-19 | 2010-01-20 | Evonik Oxeno GmbH | Verfahren zur Herstellung von tert.-Butanol |
DE10260991A1 (de) | 2002-12-24 | 2004-07-08 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von tert.-Butanol mittels Reaktivrektifikation |
-
2003
- 2003-08-22 DE DE10338581A patent/DE10338581A1/de not_active Withdrawn
-
2004
- 2004-04-07 SG SG200401999A patent/SG118238A1/en unknown
- 2004-07-02 ES ES04103134T patent/ES2397384T3/es not_active Expired - Lifetime
- 2004-07-02 EP EP04103134A patent/EP1508558B1/de not_active Expired - Lifetime
- 2004-07-19 US US10/893,306 patent/US7026519B2/en not_active Expired - Fee Related
- 2004-08-16 TW TW093124556A patent/TW200513537A/zh unknown
- 2004-08-20 CN CNB2004100578639A patent/CN100358852C/zh not_active Expired - Fee Related
- 2004-08-20 KR KR1020040065695A patent/KR101122516B1/ko not_active IP Right Cessation
- 2004-08-23 JP JP2004242901A patent/JP4504135B2/ja not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60233024A (ja) * | 1984-05-02 | 1985-11-19 | Mitsui Toatsu Chem Inc | 第3級ブチルアルコ−ルの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1508558A1 (de) | 2005-02-23 |
US7026519B2 (en) | 2006-04-11 |
SG118238A1 (en) | 2006-01-27 |
JP2005068150A (ja) | 2005-03-17 |
CN100358852C (zh) | 2008-01-02 |
KR20050020690A (ko) | 2005-03-04 |
DE10338581A1 (de) | 2005-03-17 |
CN1603290A (zh) | 2005-04-06 |
US20050043571A1 (en) | 2005-02-24 |
ES2397384T3 (es) | 2013-03-06 |
KR101122516B1 (ko) | 2012-03-15 |
EP1508558B1 (de) | 2012-10-24 |
TW200513537A (en) | 2005-04-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4504135B2 (ja) | t−ブタノールの製造方法 | |
KR101157813B1 (ko) | 이소부텐 함유 탄화수소 혼합물로부터 3급 부탄올을제조하는 방법 | |
JP5037007B2 (ja) | 単一分留カラムによる多段階オリゴマー化工法および装置 | |
RU2165955C2 (ru) | Трехстадийный способ получения легких олефинов из метана и/или этана | |
CN101573313B (zh) | 利用歧化反应将氧合物转化成烯烃 | |
EP2751056A2 (en) | A process for the production of olefins and use thereof | |
CN105837390A (zh) | 由c4烃混合物获得高纯度1-丁烯的方法 | |
KR20070070093A (ko) | 1-부텐계 스트림의 정밀 정제방법 | |
PL206182B1 (pl) | Sposób wytwarzania izobutenu na drodze rozkładu eteru metylo-tert-butylowego | |
JP4292072B2 (ja) | t−ブタノールの製法 | |
JPS637168B2 (ja) | ||
CN108002995A (zh) | 一种丙酮两步法合成甲基异丁基酮的方法及其设备 | |
JP2021031494A (ja) | 最適化蒸留によるオレフィンのオリゴマー化プロセス | |
WO2010071011A1 (ja) | 酢酸エステルの製造方法 | |
CN111073690A (zh) | 使用烯烃含量降低的流将烯烃低聚的方法 | |
KR101088407B1 (ko) | 반응성 정류를 이용한 3급 부탄올의 제조방법 | |
AU598845B2 (en) | Process for the production of isopropanol and tertiary alcohols with 4 to 5 carbon atoms | |
US4760203A (en) | Process for the production of isopropyl alcohol | |
US6620975B2 (en) | Process for making butyl ethers of glycols | |
CN110204409A (zh) | 异丁烯的制造装置以及异丁烯的制造方法 | |
CN110776389B (zh) | 一种制备苯乙烯的复配型催化剂及方法 | |
EP1421053A1 (en) | Process for the production of acetic acid c4-esters | |
CN1646467A (zh) | 由丁二烯制造丁烯基酯的方法 | |
JP2021031495A (ja) | 最適化された蒸留によるオレフィンのオリゴマー化のプロセス | |
TW200418769A (en) | Process for preparing tert-butanol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070112 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091211 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100311 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100401 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100422 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130430 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140430 Year of fee payment: 4 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
LAPS | Cancellation because of no payment of annual fees |